Photo by Winter Park Resort

Winter Park holiday rentals

We found 2,039 holiday rentals — enter your dates for availability
Select from 341 houses, 479 flats and other holiday rentals to find the perfect place for your stay in Winter Park. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Winter Park

Showing deals for:8 Jan - 15 Jan

Living area
Outdoor dining
Living area
Interior
Exceptional
(185 reviews)

Beautiful Mountain Lodge-Ski,Hike,Bike,Relax-We Are Close to it All!

Tabernash

8% off
S$5,484
for 7 nights, 1 home
S$783 per night
includes taxes & fees
Beautiful Mountain Lodge-Ski,Hike,Bike,Relax-We Are Close to it All!
Dining
Private kitchen
Upstairs loft has the best views in the whole home.
Exterior
Exceptional
(115 reviews)

Top of the Mountain Log Home with BREATHTAKING VIEWS near Winter Park, Granby

Tabernash

6% off
S$5,029
for 7 nights, 1 home
S$718 per night
includes taxes & fees
Top of the Mountain Log Home with BREATHTAKING VIEWS near Winter Park, Granby
Kids play outside and build an Igloo
Living area
Outdoor dining
Great Room dining area, stairs to loft
Exceptional
(165 reviews)

Snow Dream Family Retreat: Hot Tub, Game Room, Stocked Kitchen, Sparkling Clean!

Winter Park

6% off
S$6,928
for 7 nights, 1 home
S$990 per night
includes taxes & fees
Snow Dream Family Retreat: Hot Tub, Game Room, Stocked Kitchen, Sparkling Clean!
Open Main Level
Wrap around porch
View from Hot Tub
Hot Tub
Exceptional
(137 reviews)

Elk Court Luxury Mountain Retreat, Sleeps up to 16 people

Winter Park

8% off
S$6,276
for 7 nights, 1 home
S$897 per night
includes taxes & fees
Elk Court Luxury Mountain Retreat, Sleeps up to 16 people
Welcome to your mountain getaway!
Over-sized kitchen island for easy meal prep and serving
Gourmet Kitchen
View from Living Room window
Exceptional
(240 reviews)

5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle

Winter Park

8% off
S$7,104
for 7 nights, 1 home
S$1,015 per night
includes taxes & fees
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
Room
Private kitchen
Interior
Living area
Exceptional
(17 reviews)

Cozy mountain escape in Empire

Empire

7% off
S$2,594
for 7 nights, 1 home
S$371 per night
includes taxes & fees
Cozy mountain escape in Empire
Living area
Private kitchen
Fitness facility
Pool
Exceptional
(46 reviews)

Dog-friendly condo close to Winter Park shuttle with pool, hot tub, tennis, gym

Fraser

8% off
S$2,483
for 7 nights, 1 apartment
S$355 per night
includes taxes & fees
Dog-friendly condo close to Winter Park shuttle with pool, hot tub, tennis, gym
Private kitchen
Exterior
Interior
Bar (on property)
Wonderful
(22 reviews)

Large Upscale Retreat off Vasquez Rd. Sleeps 14

Winter Park

11% off
S$8,603
for 7 nights, 1 cabin
S$1,229 per night
includes taxes & fees
Large Upscale Retreat off Vasquez Rd. Sleeps 14
Kitchen on Main Floor
Vasquez Creek
Dining Room on Main Floor
Living Room
Exceptional
(51 reviews)

Perfect Vacation Home for Every Season in Downtown Winter Park

Winter Park

7% off
S$7,736
for 7 nights, 1 home
S$1,105 per night
includes taxes & fees
Perfect Vacation Home for Every Season in Downtown Winter Park
Interior
Hot Tub off of ski run/1st Floor (no jets)
Pole Creek Golf Course - 20 minute drive from Condo
Exterior
Exceptional
(10 reviews)

New Condo w/ Hot Tub & Balcony-Short Walk/Bike to Trestle Bike Park & Village

Winter Park

8% off
S$4,824
for 7 nights, 1 apartment
S$689 per night
includes taxes & fees
New Condo w/ Hot Tub & Balcony-Short Walk/Bike to Trestle Bike Park & Village
Exterior
Terrace/patio
Living area
Room
Exceptional
(36 reviews)

Beautiful view 2 miles above sea level

Idaho Springs

8% off
S$2,000
for 7 nights, 1 home
S$286 per night
includes taxes & fees
Beautiful view 2 miles above sea level
Outdoor dining
Beautiful modern mountain home
Large Kitchen with 3 bar stools
Room
Exceptional
(240 reviews)

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Winter Park

8% off
S$3,162
for 7 nights, 1 apartment
S$452 per night
includes taxes & fees
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park
Mary Jane Trail top
Property grounds
Dining and kitchen
Pool and hot tub at the clubhouse
Exceptional
(82 reviews)

Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!

Winter Park

8% off
S$3,973
for 7 nights, 1 apartment
S$568 per night
includes taxes & fees
Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
Open Floor Plan Living, Dining, Kitchen
Kitchen into Living Spaces
Dining & Kitchen
Interior
Exceptional
(28 reviews)

Penthouse Cozy Condo in the heart of Downtown Winter Park

Winter Park

8% off
S$4,788
for 7 nights, 1 apartment
S$684 per night
includes taxes & fees
Penthouse Cozy Condo in the heart of Downtown Winter Park
Exterior
Exterior
Living room
Room
Exceptional
(72 reviews)

Winter Park Retreat - In The Heart Of Downtown

Winter Park

7% off
S$5,184
for 7 nights, 1 home
S$741 per night
includes taxes & fees
Winter Park Retreat - In The Heart Of Downtown
Interior
Room
Interior
Property grounds
Exceptional
(15 reviews)

Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4

Winter Park

8% off
S$4,328
for 7 nights, 1 apartment
S$618 per night
includes taxes & fees
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Private kitchen
Living area
Interior
Room
Exceptional
(83 reviews)

Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

Winter Park

7% off
S$4,613
for 7 nights, 1 home
S$659 per night
includes taxes & fees
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Living area
Living area
Dining
Living area
Exceptional
(9 reviews)

Updated 1-Bedroom ski-in ski-out Condo at Winter Park

Winter Park

8% off
S$6,465
for 7 nights, 1 apartment
S$924 per night
includes taxes & fees
Updated 1-Bedroom ski-in ski-out Condo at Winter Park
Pool and indoor hot tub at the Recreation Center.
Recreation Center, outdoor hot tub
Gym at the Recreation Center.
Recreation Center Fire Place and TV
Wonderful
(62 reviews)

Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821

Winter Park

7% off
S$1,803
for 7 nights, 1 apartment
S$258 per night
includes taxes & fees
Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821
Seats for all of the family in our dining area
Bright unit with views of the resort. No binoculars required!
Huge open living room and combined dining area
Living area
Exceptional
(22 reviews)

Covered Parking, Cozy, spacious with beautiful views on the bus line

Fraser

12% off
S$3,584
for 7 nights, 1 apartment
S$512 per night
includes taxes & fees
Covered Parking, Cozy, spacious with beautiful views on the bus line
Lodge lobby
ZML Riverside building
Bedroom with king size bed and views of the mountains.
Living room with queen sleeper sofa and views.
Exceptional
(30 reviews)

Zephyr Mountain Lodge - Beautifully Renovated

Winter Park

8% off
S$4,424
for 7 nights, 1 apartment
S$632 per night
includes taxes & fees
Zephyr Mountain Lodge - Beautifully Renovated
Entry and hall to main level half bathroom and garage entrance shown on left
Balcony has a BBQ and view
Lower level bonus/family room with fireplace
Entertain in a light and bright open living space
Exceptional
(72 reviews)

Rendezvous - Majestic Views|Hike|Bike|Ski and Ski Locker Available!

Fraser

7% off
S$3,548
for 7 nights, 1 villa
S$507 per night
includes taxes & fees
Rendezvous - Majestic Views|Hike|Bike|Ski and Ski Locker Available!
Beautiful fall leaves from the balcony
Lounge area with large screen TV, pool table, kids area, business center
Indoor pool at clubhouse, plus two indoor hot tubs
Well stocked kitchen with everything you need
Exceptional
(50 reviews)

Cozy and convenient family condo in heart of downtown Winter Park

Winter Park

7% off
S$2,959
for 7 nights, 1 apartment
S$423 per night
includes taxes & fees
Cozy and convenient family condo in heart of downtown Winter Park
Family room with TV and Queen Sleeper sofa, plus futon (not pictured)
Interior
Kitchen with stools for additional seating, new appliances, and a large pantry
Exceptional
(100 reviews)

Slopeside Paradise--3 BR, 2.5 Bath 2 Minutes from the Slopes!

Winter Park

8% off
S$7,150
for 7 nights, 1 home
S$1,021 per night
includes taxes & fees
Slopeside Paradise--3 BR, 2.5 Bath 2 Minutes from the Slopes!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The cosy city of Winter Park awaits you

Enjoy the live music and other features of Winter Park. Renowned for its skiing, mountain views and snowboarding, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Winter Park

Do you want to find attractions to see during your stay? Travellers enjoy Winter Park for its skiing, snowboarding and hiking. Venture out of your cosy holiday rental and experience everything that makes Winter Park a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Winter Park Ski Resort (3.7 mi / 5.9 km)
  • Keystone Ski Resort (25.5 mi / 41.1 km)
  • Trestle Bike Park (2.5 mi / 4.1 km)
  • Pole Creek Golf Club (7.7 mi / 12.3 km)
  • Ski Granby Ranch (10.3 mi / 16.6 km)
  • Eldora Mountain Resort (10.7 mi / 17.3 km)

Exploring the mountains and other natural features in Winter Park

Whether you're an adventurous traveller or just want to appreciate the scenery, Winter Park is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Rocky Mountain National Park (29.7 mi / 47.9 km)
  • Saint Mary's Glacier (9.2 mi / 14.8 km)
  • Georgetown Lake (14.1 mi / 22.7 km)
  • Torreys Peak (16 mi / 25.8 km)
  • Lake Granby (16.4 mi / 26.3 km)
  • Loveland Pass (18.4 mi / 29.6 km)

Seasonal weather averages in Winter Park

Winter Park is well known for its skiing. If you're interested in winter sports, you might consider visiting in January, February, March or April, when snowfall averages 67 cm and temperatures average -8°C.

Travelling to and around Winter Park

The nearest airport is in Broomfield, CO (BJC-Rocky Mountain Metropolitan), located 35.7 mi (57.4 km) from the city centre.

If you'd prefer to travel by train, the main station is Winter Park Ski Resort Amtrak Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a holiday rental?
Old Town Winter Park is one of the more sought-after locations for a holiday property in Winter Park. Spend your stay here to savour the comfort and privacy that comes with having the entire place to yourself.
What is the most popular type of holiday rental accommodation in Winter Park?
The most desirable types of holiday rentals in Winter Park are condos. Prefer something different? Vrbo has numerous options to match our guests' unique requirements, so you'll see holiday homes in loads of sizes and shapes. The perfect fit is waiting for you — book yours today.
How much does it cost to rent a holiday rental in Winter Park?
Different factors affect the price of a holiday rental in Winter Park, such as the time of year, length of stay and property type. However, all our holiday homes have something in common — exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winter Park?
When you travel and the style and size of the property will determine the cost of your beachside escape. Put in your Winter Park travel dates to see your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday rentals in Winter Park?
Pack a travel bag and a bone for the pup in your life because Winter Park has 598 stays that open their doors to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Winter Park?
Tick the "pool" box in our handy filter tool and select from 255 houses with private pools in Winter Park on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo holiday home comes with a swimming pool.
What are popular rental amenities in Winter Park?
Some of the most popular rental amenities guests are looking for in Winter Park are tennis, a chef and a lake view. Whether you're travelling with family, buddies or even pets, Vrbo holiday properties feature the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Winter Park?
Winter Park has 101 holiday properties that can fit 10 or more people. These properties come with the space and privacy you need to share good times with your nearest and dearest.
Are there holiday rentals in Winter Park that welcome kids?
With 598 family-friendly holiday rentals available in Winter Park, now is a fantastic time to introduce your children to the pleasures of travel. Simply check our "Properties good for families" filter box to view stays packed with amenities perfect for families on the move, such as multiple bedrooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Winter Park?
There are plenty of amazing things to see and do with the family in Winter Park, including:
  • Amazen Maze Winter Park
  • Moffat Tunnel West Portal
  • Trestle Bike Park
Are there one-bedroom holiday rentals in Winter Park?
You'll find 106 one-bedroom properties in Winter Park to choose from. A one-bedroom holiday home is a wonderful choice if it's just you and your partner or if you're holidaying alone. Toss in more convenience, space and privacy compared to a hotel, and you're bound to have a memorable trip.
Can I find two-bedroom holiday rentals in Winter Park?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 221 two-bedroom holiday properties Winter Park has to offer.
Are there holiday rentals with WiFi in Winter Park?
Whether you want to keep up with the headlines, reply to emails or surf your social networks, there are 157 holiday homes with WiFi in Winter Park. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Winter Park?
You can pick from 27 Vrbo holiday homes with air conditioning in Winter Park giving you that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday rental in Winter Park?
We recommend checking with the Winter Park holiday rental you'd like on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Winter Park for?
How long you can rent a holiday rental in Winter Park is down to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Winter Park.

More holiday ideas